Doug's Boys
by Durotos
Summary: Greaser AU! In 1950s Mineral Town, an unsuspecting inn houses the members of a greaser gang, specifically hired to "take care of" a rival Yankee girl gang from the next town over. Tons of denim, leather, pomade, and disregard for authority, along with a bunch of hip cats that are cruisin' for a bruisin' in a turf war to end them all. Slight nods to The Outsiders & West Side Story.
1. Enter Gray

_**Author's Note: Welcome, welcome! Are y'all ready for greasers, turf wars, crooked politicians, and yankee girl gangs? This story has been bouncing around in my head for quite some time now and I'm super excited to present it to you! These first few chapters will be a little short as I introduce the main characters, but things will pick up quickly! Without further ado, enjoy!**_

0o0o0o0

He rolled his eyes as they traveled to the overly ornate emblem on the corner of the envelope; he already knew the letter's contents. Putting out his cigarette in an overcrowded ashtray, he turned the envelope over in his hands.

 _Might as well get this over with…_

The seal was ripped open and the envelope was torn haphazardly as he let out a sigh, surprised his hands were steady despite knowing what was to come.

 _Dear Grayson Iwata,_

 _This letter is to serve as your third notice of your lack of compliance of our Academy's attendance policy. As an accelerated and prestigious School of Mechanical Studies, it is vital for our students to have a presence in the classroom._

 _The Academy's guidelines clearly state in Article 5, Section B (7) that "Students who are absent five (5) or more days during a semester without official written notice will be removed from the roster list, and therefore, expelled"._

 _This letter is also notice of your termination as a student of Umbridge Mechanical Academy. We wish you the best in your academic future._

 _Sincerely,_

 _Dean Daryl Faustus_

Despite the briefness of the letter, he was still surprised he had actually read the entire thing. Upon studying the addressee once more, the young man crumpled the parchment into a ball and tossed it over his shoulder, not caring that it had landed nowhere near his wastebasket. He lit a fresh cigarette and sat on his lumpy bed with a loud creak, contemplating where to go from here.

Grayson. Gray. Son. Iwata. He hated his name – first and last.

Gray; it was the color of stormy skies. It was the tint of the dingy diner that stood on the corner of Walnut and Third Street. The very word seemed synonymous with _unclean_ or _ruined_. No one liked the color gray; it was the hue of the mold that grew on his shabby dorm room's ceiling where the tenants upstairs had their community shower. He shuddered - it was the shade of the expired bread he found stashed in a forgotten corner of his kitchenette.

That being said, he despised his last name even more. After all, he shared a name with _him_. He had been a good father at one point, but the young man preferred to forget this fact. It hurt more to remember that his old man's heart was once capable of love.

The first few courses at the academy had been painfully easy – Gray almost laughed at the notion that this was considered an accelerated, prestigious program. The basics came naturally to him; the tips and tricks his father taught him while he was growing up paid off. He was his father's son, after all.

This notion disgusted him as he made the realization of it.

It was a few semesters in when he remembered this unfortunate fact, and it consumed him. He hit a wall. Perhaps it was the material, or maybe it was the fact that he was pursuing his father's field of study… Nothing made sense anymore. It was as if the instructors had all decided to speak another language one day. The young man agonized over his books, the letters dancing about in his eyes, the formulas like a hidden code that everyone understood but him.

He never considered asking the instructors for help. That wasn't what Iwatas did. Upon this reminder that he was indeed an Iwata, the glow faded from his eyes.

What was he doing with his life, he wondered for the millionth time as he came back to his empty dorm room. Trying to live out his father's wishes? Why? He hadn't cared what his father thought for years, or so he believed… Furious, he holed himself up in his room, refusing to show up for class.

He knew that he had sealed his own fate. The only thing to figure out was where his new home would be. As long as it wasn't here, he figured he could manage somehow. It had only been a matter of time before the letter came. He had already packed.

 _ **0o0o0o0**_

 _ **Author's Note: Well, here we are at the beginning. I would love to hear what you think! This is set to be a much faster-paced story than most of my other works. Look forward to it! :)**_


	2. Enter Kai

The ocean air smelled of salt, tanning oil, and sizzling hot dogs. A familiar rockabilly song played on the radio, the melody carried out on the breeze. The sun's rays danced across the crystal blue water and the young man watched a few children playing with a ball in the water when a familiar tightness rose in his stomach.

A gruff voice startled him from his thoughts. "Oi, Kai! Go drum up some business! Our numbers are low today!"

His stomach twisted again. He knew that feeling. _Right. Jealousy._

It was a pity to live in such a beautiful place and never get to enjoy it. His eyes scanned the crowd and settled on a pair of young women lounging at a picnic table. They looked overdressed for the hot weather and had pale skin; they weren't locals, that was for certain. He forced a charming smile on his face as he made his way over to them.

"'Afternoon, ladies. Are you familiar with the boardwalk? You two look like you know how to have a swell time. What if I told ya that I could make your afternoon even better?" Kai expertly scanned the facial expressions of the potential customers. He got a mix of reactions from the women. One of them already liked what she saw and the other looked as if she was being asked to walk into a dark alley with a stranger.

"We're here on vacation. Our older sister's getting married," the more relaxed of the two explained, fluffing her short black hair.

The wary sister's eyes widened as she stared at her sibling in horror. "What do you think you're doing, giving him that kind of information? We don't know who he is or what he's like!"

"Aw, he wasn't tryin' to rattle your cage, Betty," her sister replied. "Sounds like he's just up for a little fun…" She turned toward her sister and winked. "Maybe if we're lucky, it'll include a little game of back seat bingo!"

Kai rubbed the back of his neck – he seemed to be cursed with giving the incorrect tone to his conversations. While he definitely did enjoy female company, and he wasn't a stranger to short flings with vacationers, many seemed to get the wrong idea with him – it was all starting to feel rather empty. "Ah, I'm sorry, ladies." His eyes drifted toward his father, holding a hot dog between a pair of tongs and pointing at it violently. Flustered, he stumbled over his words. "I was just wondering if you'd be interested in some weiner-"

"Oh, _get bent_!" Betty stood up and huffed away, horrified at such a proposition.

Laughing heartily, her sister watched her leave. She ran a few fingers through her dark tresses and gave Kai a flirtatious giggle. "Ah, sorry she's such a wet rag. It's gonna be a 'no' on the hot dogs for now, but maybe in a couple hours I meet ya out here at the pier?" Her green eyes glittered at him as she gave him a playful wink. "See you later, alligator."

"In a while, crocodile." Kai uttered the words automatically as his senses went numb. He trudged back to the food stand, discouraged as he awaited his punishment.

His father rapped his metal spatula on the wooden countertop loudly in frustration. "Dammit, Kai, how hard is it to sell someone a _hot dog_? You see a pair of big eyes and you can't help yourself. You lazy, good-for-nothing-"

"Stop!" His own words startled him back into reality. He had heard it too much; he could quote the entire speech. He was a lazy, good-for-nothing punk with no work ethic and wasn't interested in anything other than chasing skirts. But he wasn't, or at least he didn't think he was. He knew he could show his father he was wrong, but that was difficult to do when he constantly felt attacked.

"Get back on the grill," his father growled.

Faint memories of a happy family giggling around the dining room table caused a lump to form in his throat. Kai bit his lip. "You weren't always like this. When Mom was alive-"

"Get. The. _Hell_. Back. On. The. Grill." His face was a threatening shade of violet as he slapped the spatula loudly on the counter.

The young man turned on his heel and walked away. It just wasn't home anymore.

 _ **0o0o0o0**_

 _ **Author's Note: Thanks for following along!**_

 _ **Now that there's actually some dialogue, I decided to add a list of 50's slang that appeared in this chapter for y'all:**_

 _ **Rattle someone's cage: Deliberately try to upset someone**_

 _ **Back seat bingo: making out with someone in the back of a car**_

 _ **Get bent: equivalent to "drop dead!"**_

 _ **Wet rag: someone who is no fun**_

 _ **See you later, alligator/In a while, crocodile: this was a silly farewell (In my research, I've noticed a lot of 50's slang includes rhymes.)**_

 _ **Skirts: girls**_

 _ **Huh, I guess that was it. Well, I hope you're looking forward to more to come!**_


	3. Enter Cliff

_**Author's Note: Heads up, folks. Violence ahead.**_

 _ **0o0o0o0**_

A fresh start.

That's what Cliff would always tell himself it was, anyway. The flimsy lie got more laughable every time he moved, but he didn't care; it wasn't as if anyone really knew his past and how pathetic it was. He searched desperately for a town that gave him at least a taste of what his home felt like before things had gone south, but he was always left disappointed. Perhaps he was too picky, he told himself. Maybe he needed to just find a place and stick with it. Finding a town that reminded him of home was just selfish.

But his selfishness was the only reason he was still going today. After all, if he hadn't run away…

He would be dead, just like the rest of his family.

Cliff frowned as the memories came back to him, letting out a sigh and touching a finger to the long, thin scar that streamed down his cheek just below the outer corner of his eye. It had all been only six months ago, but it felt like an entirely different lifetime.

It was supposed to be no-man's land. The territories were well-known, and everyone knew that Harbor Street was a safe zone. It was during a dreary, cloudy afternoon that he had gone to the bus stop to pick up his mother and little sister; he had been unable to shake an uneasy feeling all day.

As he walked to his destination, a chill ran down his spine as he quickly passed a group of older teenagers slowly walking down the sidewalk, laughing and smoking cigarettes. One bumped his shoulder against Cliff's, letting out a mix between a chuckle and a sneer.

"Watch it, kiddo."

He nodded nervously and continued – being only sixteen years old himself, and more importantly, alone, he kept his distance. But that was the way he always worked: avoiding confrontation at any cost, even if he came across as a chicken.

What were the chances that the kid getting off the bus right behind his mother and sister was an Osprey Gang member that a group of nearby Bobcats was planning to jump?

Before he knew what was happening, a rumble broke out in the mix of innocent travelers and gang members; it seemed the Osprey wasn't as alone as the teenagers Cliff had walked past moments ago thought he would be. Screams and yells broke out over the sounds of cursing and blows, bike chains rattling through the air, clanking against baseball bats and broom handles. Cliff's sister went down first, a sickening crunch under the trampling of the crowd reaching his ears as a group of Ospreys ganged up on a lone Bobcat that was standing beside her. The ten-year-old girl hadn't stood much of a chance and Cliff's heart stopped as his mother fruitlessly attempted to reach her. He began to shove through the crowd and their eyes met.

"Cliff, run! Get _out_ of here!" Her voice was hoarse.

Should he obey? It was dangerous and his sister was already gone, just like that. A wave of nausea hit him as his mouth uncontrollably filled with saliva, the acid in his stomach threatening to rise up. His sister was lifeless on the ground. He didn't want to lose his mother, too. He couldn't hear anything other than the blood coursing around his ears. Cliff's feet refused to venture further into the crowd; he felt as if he was watching himself from outside of his body as his head began to spin. He remained frozen in horror as an Osprey used his mother as a shield for a Bobcat's switchblade, slashing the knife across her throat. The paper bag she was holding had fallen to the ground and she had been shoved to the side as she crumpled in slow motion, the blood streaming down the collar of her yellow dress. She disappeared into the sea of people.

 _Go to her! She needs you! You might still be able to save her!_

Cliff had felt his eyes begin to flicker, his vision quickly tunneling.

 _Run._

He had collided into a wall of denim and his eyes struggled to focus on the young man in front of him. The gang member had a good half foot on him, but Cliff knew he needed to keep moving if he was going to get away.

"Bobcat bastard!"

Cliff didn't realize that he was being addressed, as he didn't associate with gangs. He silently tried to push past and when he was denied, he felt a searing burn along the left side of his face and caught the sight of his bloody knife.

 _Run._

Mechanically, he pulled the switchblade he stored in the cuff of his boot and plunged it into the jugular of the man blocking him. He watched as the pupils of the man's eyes grew large, his hazel irises almost vanishing completely. His breathing became heavy as he stumbled and leaned into Cliff. He weighed too much; Cliff shrugged him off, flicking his blade back and stuffing it into his back pocket, too numb to be grateful that his father had taught him how to use one before he left for the war and never returned. The thug attempted to grasp Cliff out of an instinct to steady himself and was surprised when he was shrugged off once again.

"F-fuck…" His hands flew to his neck and he fell to his knees, lost in his own pain.

 _Run._

There had been two casualties that day – the only two people in Cliff's life that mattered. By the time the police had arrived, the gangs had cleared out, leaving mother and daughter in a pool of blood and strewn groceries.

Cliff didn't consider the thought of going back to school; he hadn't thought much of anything anymore. He spent the next week in solitude, locked in his bedroom. A loud knock at the front door caught his attention.

He wished he hadn't answered. The trio of boys at the door all wore the same matching gray leather jackets and cuffed baggy workpants he had grown to hate. Bobcats. He was about to close the door when a boy with a brown pompadour leaned in the doorway, a toothy grin spreading across his face.

"What's buzzin', cousin? Knew we'd find out where you were, kid. You're pretty good in a scrap, huh?"

Cliff's blood ran cold. What were they doing here? "I-I don't want any trouble."

"And we ain't lookin' to give ya any. We heard about your sister and old lady. Bad news, man."

The boy's eyes widened and became very shiny; it was their fault that this had happened in the first place. He clenched his jaw and gave a slight nod.

The trio pushed their way through the door and Cliff's heart threatened to pound out of his chest. "Nice place you got here. You all alone?"

He found himself unable to reply. Would saying yes be a death sentence?

One of his lackeys spoke up. "He ain't got no family. It was in the papers, remember?"

He got a playful elbow to the ribs as the brunette flashed Cliff a playful grin. "Sorry 'bout Paulie; he's embarrassing, really. Name's Clyde, President of the Bobcats. We saw how you took out that Osprey chump the other day – ya really razzed my berries."

"Yeah, Slick's an asshole. He's still in the hospital," the redhead Bobcat chortled.

"Anyway, we could use a kid like you. We ain't like those Osprey scum. No initiations, nothin' like that. We're family. We go out for sodas, hang out at the pleasure pit, y'know, cool stuff... Y'know… _we_ could be your family, Cliff." He looked at him with wide green eyes that almost looked… sincere?

Cliff gulped, shocked that they had learned his name.

 _Family? No… you only get one of those and they took that from me…_

Clyde smirked at his expression; Cliff was trembling. "No sweat, boy. Pile up some z's and ruminate on it for a bit. We hang at Leo's. We'll see you…" He pointed to the doorway and his two cohorts headed out. He turned back and gave Cliff a friendly nod of the head. "Cliff."

As the door closed, so had his whole world. He could feel his pulse pounding in his throat.

 _Run._

Snapping back to reality, Cliff shifted his duffel bag over his shoulder and looked at the street sign before him.

 _Mineral Town – 5 Miles_

He had no idea what was in store for him, but all he knew was that he had to move forward.

 _ **0o0o0o0**_

 _ **Author's Note: Whoops, Cliff's introduction was quite a bit longer (is anyone really surprised?). His back story is a bit darker than the rest, but I feel like he shows a lot of signs of PTSD in-game, so I felt like it was a good fit. This is the first thing I've really posted with darker elements, so I'd love to hear feedback on what you liked and what I could improve upon!**_

 _ **Wow, I didn't realize how much research I've had to do for this different era. Really random stuff, like I made sure public buses were a thing then, I replaced Cliff's backpack with a duffel bag, just little things like that. Plus the slang! I also have been learning a lot about 1950's gangs. I'm learning a lot though, and it's pretty fun! Thanks for reading, reviewing, and following along! I really hope you enjoyed! :)**_

 _ **P.S. River City Ransom fans might recognize the name of the Osprey Cliff took out. (I actually debated about having him kill a man, but I felt like that would've maybe been too much. Thoughts?)**_

 _ **1950's Slang:**_

 _ **What's buzzin', cousin? – Greeting**_

 _ **Scrap – Fight**_

 _ **Old Lady – Mother**_

 _ **Razz my berries – impress me**_

 _ **Pleasure pit - drive-in movie theater**_

 _ **Pile up some z's - sleep**_


End file.
